3-(4-氨基苯基)-5-乙基-1,2,4-噁二唑 | 10185-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(4-氨基苯基)-5-乙基-1,2,4-噁二唑
• 英文名称: 3-(4'-aminophenyl)-5-ethyl-1,2,4-oxadiazole
• 英文别名: 4-(5-Ethyl-1,2,4-oxadiazol-3-yl)aniline
• CAS: 10185-71-4
• 化学式: C₁₀H₁₁N₃O
• mdl: MFCD12191340
• 分子量: 189.217
• InChiKey: GBCCZEVTBFBSTB-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C
• 沸点：
  366.1±44.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-氨基苯基)-5-乙基-1,2,4-噁二唑 、 (rac)-6-fluoro-8-(4-methyl-piperazin-1-yl)-chroman-2-carboxylic acid hydrochloride 以to give 145 mg (35%) of product的产率得到6-fluoro-N-(4-(5-ethyl-1,2,4-oxadiazol-3-yl)phenyl)-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide
  参考文献：
  名称：

  Chroman compounds

  摘要：

  根据下面的公式（I）合成化合物： 其中R1、R2、R3和R4如规范中定义，药学上可接受的盐，制备方法，含有该化合物的制药组合物以及使用该化合物的方法。

  公开号：

  US20070135442A1
• 作为产物：
  描述：

  5-乙基-3-(4-硝基苯基)-1,2,4-噁二唑 在 sodium sulfide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.75h， 以70%的产率得到3-(4-氨基苯基)-5-乙基-1,2,4-噁二唑
  参考文献：
  名称：

  Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

  摘要：

  A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 +/- 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 +/- 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.013

文献信息

• Antiparasitic agents. 6. Synthesis and anthelmintic activities of novel isothiocyanatophenyl-1,2,4-oxadiazoles
  作者：R. D. Haugwitz、A. J. Martinez、J. Venslavsky、R. G. Angel、B. V. Maurer、G. A. Jacobs、V. L. Narayanan、L. R. Cruthers、J. Szanto

  DOI：10.1021/jm00147a019

  日期：1985.9

  The syntheses and anthelmintic activities of 31 3- and 5-(isothiocyanatophenyl)-1,2,4-oxadiazoles are reported. In the primary anthelmintic screen, 3-(4-isothiocyanatophenyl)-1,2,4-oxadiazole (39) showed 100% nematocidal activity and 3-(2-furanyl)-5-(4-isothiocyanatophenyl)-1,2,4-oxadiazole (63), 3-(2-furanyl)-5-(2-chloro-4-isothiocyanatophenyl)-1,2,4-oxadiazole (64), and 3-(2-furanyl)-5-(4-chloro-3-isothiocyanatophenyl)-1,2,4-oxadiazole (66) showed 100% taeniacidal activity when administered orally to mice. The two most active members of this series, 39 and 63, were active against the gastrointestinal nematodes of sheep at 100 mg/kg. In addition, 39 was also found to be active against hookworms in dogs at a single, oral dose of 200 mg/kg.
• [DE] OXADIAZOLYL-U. THIADIAZOLYL-BENZOYLHARNSTOFFE UND IHRE VERWENDUNG ALS SCHÄDLINGSBEKÄMPFUNGSMITTEL<br/>[EN] OXADIAZOLYL AND THIADIAZOLYL BENZOYL UREAS AND THE USE THEREOF AS PESTICIDES<br/>[FR] OXADIAZOLYL BENZOYL UREES ET THIADIAZOLYL BENZOYL UREES ET LEUR UTILISATION EN TANT QUE PESTICIDES
  申请人：BAYER AG

  公开号：WO2003016293A1

  公开（公告）日：2003-02-27

  Die vorliegende Erfindung betrifft neue Oxadiazolyl- und Thiadiazolyl-benzoylharnstoffe der Formel (I) in welcher R?1, R2, R3¿, n und Het die oben angegebene Bedeutung haben,Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel.
• [EN] CHROMAN COMPOUNDS AS 5 -HTlB ANTAGONISTS<br/>[FR] COMPOSES CHROMANE UTILISES EN TANT QU'ANTAGONISTES DES 5-HT1B
  申请人：ASTRAZENECA AB

  公开号：WO2007053094A1

  公开（公告）日：2007-05-10

  [EN] Chroman derivatives according to Formula (I) below: wherein R¹, R², R³ ,and R⁴ are as defined in the specification, pharmaceutically-acceptable salts, methods of making, pharmaceutical .compositions containing and methods for using the'' same. The compounds are 5-HT_1B antagonists and are useful in the treatment of mood and . anxiety disorders as well as cognitive disorders.
  [FR] L'invention concerne des dérivés de chromane de formule (I) dans laquelle R¹, R², R³, et R⁴ sont tels que définis dans la description, des sels pharmaceutiquement acceptables de ces dérivés, des procédés de production correspondants, des compositions pharmaceutiques les contenant, ainsi que des procédés d'utilisation desdits composés. Ces composés sont des antagonistes des 5-HT_1B et peuvent servir à traiter les troubles de l'humeur et les troubles anxieux, ainsi que les troubles cognitifs.
• Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides
  作者：Daniel Conole、Thorsten M. Beck、Morgan Jay-Smith、Malcolm D. Tingle、Charles T. Eason、Margaret A. Brimble、David Rennison

  DOI：10.1016/j.bmc.2014.02.013

  日期：2014.4

  A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 +/- 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 +/- 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure. (C) 2014 Elsevier Ltd. All rights reserved.
• Chroman compounds
  申请人：Bernstein Peter

  公开号：US20070135442A1

  公开（公告）日：2007-06-14

  Compounds according to Formula (I) below: wherein R 1 , R 2 , R 3 , and R 4 are as defined in the specification, pharmaceutically-acceptable salts, methods of making, pharmaceutical compositions containing and methods for using the same.

  根据下面的公式（I）合成化合物： 其中R1、R2、R3和R4如规范中定义，药学上可接受的盐，制备方法，含有该化合物的制药组合物以及使用该化合物的方法。